31677-93-7

Basic information

• Product Name: Bupropion hydrochloride
• Synonyms: (+-)-alpha-tert-butylamino-3-chloropropiophenonehydrochloride;1-propanone,1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-,hydrochloride,;2-(tert-butylamino)-3’-chloro-,hydrochloride,(+-)-propiophenon;m-chloro-alpha-tert-butylaminoprophenonehydrochloride;wellbatrin;zyban(pharmaceutical);BUPROPION HCL;BUPROPION HYDROCHLORIDE
• CAS NO: 31677-93-7
• Molecular Formula: C13H19Cl2NO
• Molecular Weight: 276.2
• EINECS: 250-759-9
• Product Categories: Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor;Amines;API;Isotope;Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals;WELLBUTRIN
• Mol File: 31677-93-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 233-234 °C
• Boiling Point: 334.8 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: white/solid
• Density: ==
• Vapor Pressure: 0.000125mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: ethanol: 193 mg/mL solutions may be stored for several days
• Water Solubility: Soluble in water (>25 mg/ml), ethanol 193mg/ml, 0.1 N HCl 333 mg/ml
• CAS DataBase Reference: Bupropion hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Bupropion hydrochloride(31677-93-7)
• EPA Substance Registry System: Bupropion hydrochloride(31677-93-7)

Safety Data

• Hazard Codes: Xn,Xi,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 36-45-36/37-16-7
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: UG8858000
• Hazardous Substances Data: 31677-93-7(Hazardous Substances Data)

Usage

Chemical Properties

Bupropion hydrochloride powder is white, crystalline, and highly soluble in water. It has a bitter taste and produces the sensation of local anesthesia on the oral mucosa.

Originator

Bupropion hydrochloride,AroKor Holdings Inc.

Uses

Bupropion hydrochloride is indicated for the treatment of MDD. Bupropion hydrochloride SR (Zyban) is indicated as an aid to smoking cessation treatment.

Drug interactions

Relatively few data are available on interactions of bupropion hydrochloride with other drugs. Increased adverse experiences were reported when the drug was administered concomitantly with l-dopa. MAOIs may increase the acute toxicity of bupropion. Although bupropion is not metabolized by the CYP2D6 enzyme, the drug and its metabolite, morpholinol, inhibit this enzyme in vitro. Therefore, extreme caution should be exercised when coadministering any drug metabolized by that enzyme, and initial dosage of the drug should be as low as possible.

Brand name

Wellbutrin (GlaxoSmithKline); Zyban (GlaxoSmithKline).

Therapeutic Function

Antidepressant; Smoking cessation aid

Biological Activity

Non-selective inhibitor of dopamine and noradrenalin transporters (K i values are 1.4, 2.8 and 45 μ M for NET, DAT and SERT transporters respectively). Also inhibits neuronal nicotinic acetylcholine receptors. Displays antidepressant activity and augments nicotine self-administration at low doses in vivo .

Side effects

Bupropion hydrochloride can cause serious side effects. The most common side effects of Bupropion hydrochloride include:headachedizzinessdry mouthsore throatnauseaconstipationtrouble sleeping

Mode of action

The exact mechanism of the antidepressant action of bupropion is not known, but is presumed to be related to noradrenergic and/or dopaminergic mechanisms. Bupropion is a relatively weak inhibitor of the neuronal reuptake of norepinephrine and dopamine, and does not inhibit the reuptake of serotonin. Bupropion does not inhibit monoamine oxidase.

InChI:InChI=1/C13H18ClNO.ClH/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10;/h5-9,15H,1-4H3;1H/t9-;/m0./s1

Upstream product

• 34911-51-8 2-bromo-3'-chloropropiophenone 
• 34841-35-5 3'-chloro-propiophenone 
• 92264-82-9 (R,R)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol 
• 75-64-9 tert-butylamine 
• 34841-39-9 bupropion 

Downstream Products

• 92264-82-9 (S,S)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol 
• 92264-82-9 (R,R)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol 
• 905818-69-1 bupropion hydrobromide 

Relevant articles and documents

Convenient and scalable process for the preparation of bupropion hydrochloride via efficient bromination of m-chloropropiophenone with n-bromosuccinimide

A convenient, scalable, and commercially viable process for the production of the antidepressant drug bupropion hydrochloride (1) is reported. The process relies upon an improved, large-scale synthesis of the key intermediate, m-chloro-bromopropiophenone (4). During process development, bromine was replaced with N-bromosuccinimide (NBS) in the presence of para-toluene sulfonic acid (p-TSA), for the bromination of m-chloropropiophenone (3), in either a very low volume of acetonitrile or under solvent-free conditions, to furnish 4. Intermediate 4 was further reacted with t-butylamine in N-methyl-2-pyrrolidinone (NMP) to afford bupropion free base (5), followed by treatment with a saturated solution of hydrochloric acid in isopropyl alcohol (IPA-HCl) to afford bupropion hydrochloride (1). This improved process provides pure bupropion hydrochloride (1) in good yields and at considerably lower cost than existing processes, and it does not involve the use of hazardous reagents. Copyright

Preparation method of bupropion hydrochloride

The invention discloses a preparation method of bupropion hydrochloride. M-chlorophenylacetone is used as a raw material to take bromination reaction with sodium bromide, sulfuric acid and hydrogen peroxide in a water-halohydrocarbon solvent to prepare a brominated intermediate; then the prepared bromide reacts with tert-butylamine to prepare amfebutamone, after the reaction for preparing amfebutamone is completely reacted, the water is directly added, after a reaction solution is layered, the layered organic layer is cleaned and distilled to obtain amfebutamone, and obtained amfebutamone is acidified by virtue of isopropanol hydrochloride to obtain bupropion hydrochloride; and the peparation process of amfebutamone, the alkalinity of a water layer obtained after the layering of the reaction solution is adjusted by using sodium hydroxide, after tert-butylamine is recovered in a distillation manner, the water layer comprising bromine ions is concentrated, the pH value is adjusted to beneutral by using sulfuric acid, the obtained aqueous solution comprising sodium bromide is used for taking the bromination reaction again so as to be circularly utilized. By adopting the preparation method, the environment-friendly circular utilization of bromine is realized, and the production cost is reduced.

COMPOSITIONS AND METHODS FOR TREATING DEPRESSION, ADHD AND OTHER CENTRAL NERVOUS SYSTEM DISORDERS EMPLOYING NOVEL BUPROPION COMPOUNDS, AND METHODS FOR PRODUCTION AND USE OF NOVEL BUPROPION COMPOUNDS AND FORMULATIONS

Compositions and methods are disclosed using a purified (R)(-) enantiomer of bupropion to treat central nervous system disorders with fewer side effects compared to those seen in subjects treated with racemic bupropion. Additionally disclosed are methods and intermediates for producing enantiomerically purified (R)(-) bupropion, stable pharmaceutical formulations of (R)(-) bupropion, and pharmaceutical products and kits comprising (R)(-) bupropion for clinical use.